PMID- 12742511
OWN - NLM
STAT- MEDLINE
DCOM- 20030711
LR  - 20190702
IS  - 0027-5107 (Print)
IS  - 0027-5107 (Linking)
VI  - 537
IP  - 1
DP  - 2003 May 9
TI  - Correlation of antimutagenic activity and suppression of CYP1A with the 
      lipophilicity of alkyl gallates and other phenolic compounds.
PG  - 101-8
AB  - Alkyl gallates are widely used as food antioxidants. Methyl, ethyl, propyl, 
      lauryl, and cetyl gallates showed antimutagenicity to activated 2-aminoanthracene 
      (2AA)-induced SOS responses in Salmonella typhimurium TA1535/pSK1002. They also 
      exhibited a suppressive effect on 3-methylcholanthrene (3-MC)-induced cytochrome 
      P450 1A (CYP1A) in human hepatoma HepG2 cells, as indexed by the 
      7-ethoxyresorufin-O-deethylase (EROD) activity, and on CYP1A protein level. Both 
      antimutagenicity and suppression of CYP1A appeared to be dependent on alkyl chain 
      lengths, which suggested lipophilicity dependence. Based on those results, we 
      investigated 26 other phenolic compounds for their lipophilicity, 
      antimutagenicity and inhibition of EROD activity. The lipophilicity correlated 
      well with the inhibition of EROD activity (r=0.78), and the inhibition of EROD 
      activity correlated with the antimutagenicity of those compounds (r=0.71). The 
      results suggest that the lipophilicity of the phenolic compounds may be an 
      important factor in their ability to inhibit EROD activity.
FAU - Feng, Qing
AU  - Feng Q
AD  - Laboratory of Food and Biodynamics, Graduate School of Bioagricultural Sciences, 
      Nagoya University, 464-8601, Nagoya, Japan.
FAU - Kumagai, Takeshi
AU  - Kumagai T
FAU - Nakamura, Yoshimasa
AU  - Nakamura Y
FAU - Uchida, Koji
AU  - Uchida K
FAU - Osawa, Toshihiko
AU  - Osawa T
LA  - eng
PT  - Journal Article
PL  - Netherlands
TA  - Mutat Res
JT  - Mutation research
JID - 0400763
RN  - 0 (Anthracenes)
RN  - 0 (Antioxidants)
RN  - 0 (Mutagens)
RN  - 0 (Phenols)
RN  - 339NCG44TV (Phenol)
RN  - 632XD903SP (Gallic Acid)
RN  - 8240818JGU (2-anthramine)
RN  - EC 1.14.14.1 (Cytochrome P-450 CYP1A1)
RN  - EC 1.14.14.1 (Cytochrome P-450 CYP1A2)
SB  - IM
MH  - Anthracenes/pharmacology
MH  - Antioxidants/*chemistry/pharmacology
MH  - Cell Line
MH  - Cytochrome P-450 CYP1A1/*genetics/metabolism
MH  - Cytochrome P-450 CYP1A2/*genetics/metabolism
MH  - Gallic Acid/pharmacology
MH  - Humans
MH  - Immunoblotting
MH  - Models, Chemical
MH  - *Mutagens
MH  - Phenol
MH  - Phenols/pharmacology
MH  - Salmonella typhimurium/metabolism
MH  - Tumor Cells, Cultured
EDAT- 2003/05/14 05:00
MHDA- 2003/07/12 05:00
CRDT- 2003/05/14 05:00
PHST- 2003/05/14 05:00 [pubmed]
PHST- 2003/07/12 05:00 [medline]
PHST- 2003/05/14 05:00 [entrez]
AID - S1383571803000573 [pii]
AID - 10.1016/s1383-5718(03)00057-3 [doi]
PST - ppublish
SO  - Mutat Res. 2003 May 9;537(1):101-8. doi: 10.1016/s1383-5718(03)00057-3.